Gary's Gulch

Election Day is November 3rd, and in this short episode I make the case that this midterm is about our children's future, so have a plan to vote as early in the day as you can and bring friends with you. Then I take a one-liner I heard from Dave Ramsey, save $1,000 a month for 15 years and you'll have $500,000, and I run the math. It only works if a 12% return shows up every single year, and when I ran 100 tries with real-world ups and downs, it reached $500,000 only 28 times. Key Takeaways This midterm is about our children's future, so vote on Election Day, November 3rd, as early in the day as you can, and consider taking the day off. Find the neighbors and friends who haven't voted, and give them a ride to the polls. Saving $1,000 a month for 15 years reaches $500,000 only if you earn about 12% every single year. An average return is not an actual return: the same 12% average dropped to about $402,000 with one bad year, and 100 simulated tries reached $500,000 only 28 times. Build certainty at the bottom first, then invest in things you control, so taking risk never touches your family's future. Keywords Gary's Gulch, Gary Pinkerton, 2026 midterm elections, vote early, Election Day November 3, bring friends to the polls, Dave Ramsey, $1,000 a month retirement, save $500,000 in 15 years, 12% average return, average vs actual return, sequence of return risk, Monte Carlo simulation, retirement planning, Social Security, S&P 500, hierarchy of wealth, certainty, financial planning Episode Highlights [00:00:00 - 00:01:00] Gary is traveling, recording ahead, and predicting that early voting is working. [00:01:00 - 00:02:00] Why Gary says the stakes are bigger than party, and why we can debate ideas again in two years. [00:02:00 - 00:03:00] Vote as soon as possible on November 3rd, consider taking the day off, and give friends and neighbors a ride. [00:06:00 - 00:07:00] About $13 more a week than at $3, and the tariffs and $5,000 per adult Gary says are coming. [00:08:00 - 00:09:00] The financial calculator says $1,000 a month to $500,000 in 180 months needs about 11.9%. [00:10:00 - 00:11:00] A 15-year S&P 500 period averaging about 12% grows to $501,000 only if every year is the same. [00:11:00 - 00:12:00] The same 12% average with a 6.5% final year yields 9.55% and about $402,000, and order changes the result. [00:12:00 - 00:13:00] Counting success only at $500,000 or higher, Gary's plan got there 28 times out of 100. [00:13:00 - 00:14:00] A lifetime of financial decisions can't be fixed with one quick trick. [00:15:00 - 00:16:00] Gary's submarine command tour, the money he lost, and the five years it cost him with his kids. [00:16:00 - 00:17:00] If it only works 90% of the time, would you get on the plane? Why quick answers put you at risk, not the advisor. [00:17:00 - end] The hierarchy of wealth, investing in what you control, and the closing call to vote.  

I came across some exceptional advice from Kristin Assaad, an attorney and business coach, and I was compelled to share it here because it speaks directly to agency and to success in your family's finances. Her five numbers are ROI, cash flow, customer acquisition cost against lifetime value, your break-even point, and the cost of your own time. In this episode I walk through each one and show why they apply whether or not you own a business, because your family's finances are your most important business. Key Takeaways Your family's finances are your most important business, so run every investment and money decision through the same five numbers. Return on investment only tells the truth when time is in it, so ask how much comes back and how long it takes. Profit and cash flow are not the same thing, and liquidity is what lets you survive a downturn and negotiate from strength. Weigh the cost of acquiring a customer, or bringing on a team member, against lifetime value, and know your break-even point so you decide on math instead of emotion. Put a price on your own time, and if doing it yourself isn't beating the experts or the index, hire the help and buy your time back. Links & Resources Gary Pinkerton: http://garypinkerton.com/ Email Gary: [email protected] Kristin Assaad: https://www.kristinassaad.dk/ Kristin Assaad on LinkedIn: https://www.linkedin.com/in/kristin-assaad-andersen-9632b36a/ 5 Things You Need To Know Before Starting a Business (Level Up podcast, episode 47): https://open.spotify.com/episode/1ncjAp7pDspjK0kr0n7QOx?si=H6docut8TJO5qPp228OAzw Keywords Gary's Gulch, Gary Pinkerton, 5 numbers before starting a business, know your numbers before investing, return on investment, internal rate of return, time value of money, opportunity cost, profit vs cash flow, liquidity, customer acquisition cost, customer lifetime value, break-even point, cost of your time, agency, family finances, family office, Kristin Assaad, Level Up podcast, financial control Episode Highlights [00:00:00 - 00:01:00] Gary credits Kristin Assaad, an attorney and Level Up podcast host, and explains why a title about starting a business applies to every listener. [00:01:00 - 00:02:00] Not understanding the numbers means you don't control the business, and that is agency. [00:02:00 - 00:03:00] Why Gary prefers internal rate of return, and how a 20% return locked up for 20 years isn't what it sounds like. [00:03:00 - 00:04:00] A showroom Buick Grand National GNX and what $45,000 in 1988 dollars looks like today. [00:04:00 - 00:05:00] A return needs to be more than a dollar back, and time value of money belongs in the math. [00:05:00 - 00:06:00] Two investors, one dollar each, and why the timing of the money coming back changes everything. [00:06:00 - 00:07:00] An oil and gas deal where the deduction is the early return and 20 years to get back $100K isn't great. [00:08:00 - 00:09:00] The newer car, the bigger house, and when spending on a family experience is the better investment. [00:10:00 - 00:11:00] Liquidity lets you survive a downturn and negotiate from strength, plus tier one of the Family Office 360 hierarchy of wealth. [00:11:00 - 00:12:00] As you move up the tiers you trade certainty for opportunity, and liquidity gets you through the unexpected. [00:13:00 - 00:14:00] The time and money Gary invests in relationships, and the fees of a team you bring into your family office. [00:14:00 - 00:15:00] Why a recurring customer can outweigh what it cost to win them. [00:15:00 - 00:16:00] $2,000 to earn $10,000 of value versus $2,000 for a one-time $1,500 sale: you can't make that up on volume. [00:18:00 - 00:19:00] How valuing your own time at zero locks you inside the business you created. [00:20:00 - 00:21:00] Take back the time you're spending on active trading if the numbers don't justify it. [00:21:00 - end] The value of a competent team, and where to find Kristin and her Level Up podcast.  

Executive Summary The mainstream media is ablaze with disheartening poll results for conservatives, and my advice is simple: ignore them and go vote. In this episode I make the case that great leadership beats statistics, explain why the party in power usually watches its own voters stay home in a midterm, and lay out why voting early protects your vote, frees up scarce campaign resources, and signals to leadership who still needs a push. Over half the country can vote right now, so grab 10 friends and bank your vote. Key Takeaways Ignore the misleading polls and look at the strength of the movement, because leadership defies statistics the way underdogs defy the odds. The party in power typically sees a big drop in its own midterm turnout, so conservatives need to act as if the president is on the ballot. Voting early protects you from a work or personal emergency, bad weather, and disruptions like water main breaks or power outages at polling stations on November 3rd. Once you have voted, volunteers and the RNC can focus their limited money and time on the people who haven't. Over half the country can vote now and more than 80% will be able to next week, so take 10 friends and vote early. Keywords Gary's Gulch, Gary Pinkerton, vote early, early voting, 2026 midterm elections, midterm voter turnout, ignore the polls, misleading polls, in-person early voting, early voting by state, conservative voters, get out the vote, Election Day, November 3 midterms, leadership, underdog, RNC, hold the House and Senate, America first, bank your vote Episode Highlights [00:00:00 - 00:01:00] Gary asks what role leadership plays in America right now and says it matters more than polls and doomsday talk. [00:03:00 - 00:04:00] A true leader gets citizens to take action, so ignore the polls and see the strength of the movement. [00:05:00 - 00:06:00] The case for early voting: you can't miss Election Day, and you get more choice of days and places. [00:06:00 - 00:07:00] Early voting brings certainty and protects against water main breaks and power outages at polling places. [00:08:00 - 00:09:00] How early in-person votes get counted and released when Election Day begins, using Florida as the example. [00:10:00 - 00:11:00] A story from Peru, where voting is mandatory, and why early votes help put resources where they matter. [00:11:00 - 00:12:00] Which states have early voting open now and which open within the week. [00:15:00 - 00:16:00] Signal to the RNC and volunteers that you've voted so they can focus on your neighbors and friends. [00:17:00 - end] The final ask: vote as early as you're allowed, bring 10 friends, and make it publicly known.  

Most people use the words legacy and inheritance as if they mean the same thing. Gary draws a hard line between them: inheritance is the assets you pass on, and legacy is what you leave inside the people you've influenced, the ideals, standards, and work ethic that decide what they do with those assets. In this episode he shares real client stories, a parable about earning a dollar, and a practical case for spending time with the people you want to carry the torch. Key Takeaways An inheritance is the assets you pass on, while legacy is the ideals, standards, and work ethic you leave inside the people you've influenced. Your estate documents protect the inheritance from taxes, creditors, and poor decisions, and they help the next generation receive the baton instead of dropping it. Money is like gasoline: in the right hands it fuels a family's best moments, and in the wrong hands it burns things down. The "shirtsleeves to shirtsleeves" cycle starts when later generations never see what it took to earn the money. Kids want time with you far more than they want your money, so design your life and work around that time. Links & Resources Gary Pinkerton: garypinkerton.com Email Gary: [email protected] Also referenced in the episode: The Ronald Reagan Foundation and Library, mentioned as an example of a legacy that keeps inspiring (no link provided) Family Board Meetings, a group run by a friend of Gary's that pairs a single parent and a single child (no link provided) Keywords Gary's Gulch, Gary Pinkerton, legacy vs inheritance, what is legacy, legacy planning, estate planning, generational wealth, multi-generational wealth, shirtsleeves to shirtsleeves, inheritance planning, irrevocable trust, living trust, family legacy, passing wealth to children, teaching kids about money, family office, wealth building, financial freedom, mentorship legacy, Paradigm Life Episode Highlights [00:00:00 - 00:01:00] Gary explains why legacy is misunderstood, even in his own industry. [00:01:00 - 00:02:00] He defines inheritance as any asset you hand down, from a trust to a broken-down old car. [00:02:00 - 00:02:40] Legacy is the baton in a relay race, and your documents help the next runner receive it. [00:02:40 - 00:03:30] Building the inheritance means protecting it from taxes, creditors, and quick spending. [00:03:30 - 00:05:00] Gary compares money to gasoline: a great resource that can also burn things down. [00:05:00 - 00:07:00] A real estate investor client is sued repeatedly by his sister after their mother dies. [00:07:00 - 00:08:50] Another client's sister, named sole executor, stalls the sale of the estate's assets. [00:08:50 - 00:09:40] Gary explains how three-generation "shirtsleeves to shirtsleeves" wealth loss begins. [00:09:40 - 00:12:15] A father teaches his son to earn a dollar by throwing the unearned ones into the fire. [00:12:15 - 00:14:00] Our kids were born on first base and our grandkids on third, so how do we teach the value? [00:14:00 - 00:14:20] Families that last for generations spend real time around their children. [00:14:20 - 00:15:30] Gary's big takeaway: kids want time with you far more than they want your money. [00:15:30 - 00:17:15] Family trips of their choosing and one-on-one Family Board Meetings build the bond. [00:17:15 - 00:18:00] Gary says "I choose not to spend time with you" to keep himself honest about his priorities. [00:18:00 - 00:19:15] Agency lets you build a life and business your family can learn from and share. [00:19:15 - 00:20:10] Legacy reaches mentees too, and it can live on in books, buildings, and foundations. [00:20:10 - 00:20:30] Gary closes the episode and sends listeners off to make something amazing happen.  

In this episode, Gary Pinkerton delivers a direct call to action ahead of the general election, urging listeners, regardless of party, to vote and to bring friends and family to the polls with them. He makes the case that this election matters whether or not your preferred candidate made it through the primary, and encourages conservatives, moderates, independents, and even uneasy Democrats to prioritize voting rather than sitting out of frustration or protest. Along the way, Gary shares his own political and economic opinions, including his views on taxation, the size of government, and personal financial accountability, and references commentary from other public figures to support his position. This episode is Gary's personal political opinion and commentary, not independent reporting. A number of claims, statistics, and characterizations discussed in the episode reflect Gary's own point of view rather than verified facts, and listeners are encouraged to research anything they want to rely on for themselves. Links & Resources Mentioned No links or resources were provided for this episode. Keywords general election, voter turnout, get out the vote, civic engagement, political opinion, conservative commentary, vote early, political podcast, Gary Gulch, election season, American values, political commentary, grassroots politics, voter mobilization, personal responsibility, economic policy, Gary Pinkerton Episode Highlights [00:00:00 - 00:02:00] Gary opens with a direct call to action on voting in the upcoming general election, framing it as bigger than party lines. [00:02:00 - 00:05:00] He shares his personal take on taxation, government size, and personal financial accountability. [00:05:00 - 00:08:00] Gary urges conservatives not to sit out the election and argues turnout will be decisive. [00:08:00 - 00:11:00] He shares his opinion-based view of the current administration's economic track record. [00:14:00 - 00:16:00] Gary closes with an appeal to vote early, bring others along, and stay engaged.